Bikepacking the Oregon Outback Trail: Pro Tips & Lessons Learned

Day 1: “Follow your nose”

As these things go, day one was unlike the days that would follow. We managed to stay mostly in the eye of the surrounding weather, getting spit on occasionally but generally avoiding the nasty stuff. At lunch time we rolled into a one street town and noticed a parking lot full of rigs at the local community center. Barbecue filled the air, and instincts set in. Minutes later—after receiving a family donation rate—we were heads down in a plate of brisket, baked potato, and cake, with folksy tunes coming from a live band of local characters just feet away. Stay curious, and trust your nose, you guys.

• 10 hours on a bike feels like 10 hours on a bike, there’s no getting around that one
• If you see a full lot in a small town, check it out
• A $5 brisket, baked potato, slaw, and cake lunch can’t be beat
• Spin, don’t push—a lesson bestowed to us over a gas station dinner of beer and cookies by a 60-year-old Jackson Hole resident turned part time Oregon pot farmhand. It would become a mantra for the entire trip. When someone who’s been cycling across the West since the 70s (and hasn’t owned a car in just as long) drops some casual knowledge, do your best to listen.
  

Day 2: “How are we still climbing?”

On the second day we woke to rain, maybe even a snow flurry. Had I known what was to come, I would’ve hunkered down in our MSR tent and refused to move. But I didn’t, so we hit the road with sights set on the Cowboy Dinner Tree, a legendary reservation-only restaurant some 55 miles ahead where the only thing on the menu is either a 30oz steak or a whole roasted chicken. In between waking and stumbling into CDT with shoes sloshing with water a lot of miserable shit happened—most notably a lot of rain, low 40 degree temps, and seemingly endless rolling hills.

Throughout the day I tried to think on what I had done in my life that was more difficult than this at that exact moment. I’ve done a lot of gnarly shit, but nothing came to mind. The only reason I rated this day a 9/10 was because I didn’t quit. Though had Uber been an option, there’s a serious chance I woulda taken it.

• If you have a reservation to meet, you’ll rider harder
• A 30oz steak won’t make up for a rainy day in hell, but it’ll sure take your mind off it for a few mins
• It is possible to have a net loss in elevation and still spend the entire day climbing
• Chamois butter might seem gross, but it does the trick
• 5 minutes spent laying down beats 15 of resting on your feet
• Can’t take the soup with you
• Don’t feel bad about making a smart decision to save the trip (shout out Silver Lake Mercantile for putting us up for the night after one of the trip’s most defeating days)

Day 3: “The Red Sauce ain’t shit”

Day three welcomed us with 50 mph headwinds, but thankfully some sunshine too. All reports stated this day would be the most difficult, with 20 miles of quicksand-like lava rock nicknamed the “Red Sauce” capping off the day's milage. We struggled to make process early on, averaging just 4 miles an hour due to the tremendous wind, but for once luck was on our side as we approached the volcanic zone—turns out the biblical rain that we’d encountered the day before packed down the sauce, making it into a rather lovely red road ripe for the ripping. Still, we didn’t hit our mileage goal, again.

• Leftover steak and eggs made in a tiny hotel room microwave is actually a pretty nice way to start a day
• Hydro Flasks may be heavier than single-wall bottles, but when the sun is out cold water is worth the weight of insulation
• It’s OK to not to meet your mileage goal
• Wind is worse than hail, but still probably not as bad as rain
• Never pass up an opportunity to refill water supplies
• Don’t settle for a shitty campsite / the best campsites take a bit of effort to find
• Even 30 minutes beside a campfire is enough to bring a trampled spirit back to life
• Cougars are big cats and use signs as scratching posts

Day 4: “Take us to the bike shop with beer”

Day four was a highlight. We finally had some mellow miles (not a ton, but a few), got to fly the drone a bit, wet a fly, and even catch up with family—the other three boys in the gang had their respective wives meet them to resupply Honey Stinger waffles and Clif jelly things. In addition to being perfectly located for our rendezvous, Prineville is also home to Good Bike Co, a dang impressive bike shop with coffee, beer on tap, and a map reading room for figuring out where the hell you are or for planning the next adventure, and Tastee Treet, a 1950’s era holdover burger joint serving the best (and biggest) burgers, shakes, and ice cream in the state. In hindsight this day was the easiest.

• A gnarly hill is better tackled first thing in the morning than last thing at night
• If a stranger invites you to stay on their ranch, do it
• Don’t be afraid to accept the kindness of strangers
• Sometimes three patties on a burger is just the right number
• Always get dessert
• Wind can make a descent feel like a climb
• Coffee is good at all hours

Day 5: “She thinks you're crazy, and I think you’re idiots!”

After a long morning of epic gravel descents and an extended afternoon (and evening) of dusty, soul crushing climbs we found ourselves running dangerously low on water. With the next closest “town” lacking a store of any kind, we sent our resident Good Ol’ Boy to knock on a door and ask for water. Not only did he deliver on water, but the interaction quickly became a genuine highlight of the trip as we ended up sharing a couple warm beers with two aging 8th generation Oregonians—the old man’s great grandfather had homesteaded the very land we stood on in the mid 1800s. Even in the current political climate, deep in Trump country, we found common ground in humor, sports talk, and simple neighborliness.

• Pack real food, not just bars
• Look before you leap—the second river crossing of four nearly took one overzealous member of the crew out of commission with a submerged boulder. As Beau launched ass over tea kettle at full speed in easily the most remote section of the trail, there was nothing to do but watch and say a silent prayer. Amazingly, he walked away bike and body unscathed, though soaked to the bone
• Climbing 4500’ over 58 miles sucks
• To-go berry cobbler is good even after 24 hours and 40 miles spent strapped to a bike
• There’s a difference between being athletic and being an athlete
• No shame in granny gear

Day 6: “It’s never actually going to get easier, is it?”

We awoke at sunup on the final day, knowing we would have to make up for every day prior that we hadn't hit our mileage goals (every day). With 71 or so miles to go we launched into the day with one doozy of a climb followed by a stretch on the highway where we encountered the trip’s first flat. Then another. And then another, a few minutes later. Three flats in an hour. They say “better late than never,” but that doesn’t apply to flats.

• Bring multiple spare tubes + extra pump
• If you don’t like the rain, don’t worry, the hill climbs will distract you
• Don't assume someone else is carrying your spares—be responsible for yourself
• A 29er inner tube will run on a 650b tire if need be
• Don’t pass up a chance to buy beer. You may not want it then, but later you will
• Saving the biggest day for last is OK if it makes the previous days manageable
• On the Oregon Outback, don’t assume the days will get easier, because they won’t

Final Lesson Learned: No matter how difficult the terrain, defeating the weather, or exhausted you feel, being on a genuine adventure sure beats the h*ck out of sitting in front of a computer.